Tetrabutylammonium Fluoride → HCID 58514462, compound

Participants

Reaction Steps

At Room Temperature and Under Inert Atmosphere, 1.0 M TBAF in THF (1.75 mL, 5 equiv.) was added a solution of 30 (181 mg, 0.35 mmol) in anhydrous THF (16 mL). The solution was refluxed for 4 h. The resulting mixture was then cautiously quenched at 0° C. with H2O. The mixture was extracted with EtOAc (3×20 mL). The resulting organic layers were dried over MgSO4, filtered, and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (eluent: CH2Cl2/EtOAc 7:3 to EtOAc) to afford R313 in 61% yield as a yellow solid; 1H-NMR (300 MHz, DMSO-d6): δ 12.05 (bs, 1H), 8.75 (d, 1H, J=2.4 Hz), 8.55 (d, 1H, J=1.7 Hz), 8.43 (d, 1H, J=2.4 Hz), 7.81 (dd, 1H, J=1.7, 8.7 Hz), 7.70 (d, 2H, J=8.1 Hz), 7.58 (d, 1H, J=8.7 Hz), 7.41 (d, 2H, J=8.1 Hz), 3.59 (t, 4H, J=4.4 Hz), 3.51 (s, 2H), 2.39 (t, 4H, J=4.4 Hz); 13C-NMR (75 MHz, DMSO-d6): δ 150.6 (C), 144.2 (C), 139.5 (C), 139.2 (C), 136.3 (C), 132.3 (C), 129.6 (2 CH), 128.3 (C), 126.5 (2 CH), 126.4 (CH), 121.8 (C), 120.2 (C), 119.8 (CH), 116.7 (C), 111.9 (CH), 66.2 (2 CH2), 62.1 (CH2), 53.2 (2 CH2); MS (ESI) m/z 378 [M+H+]

Provenance & Evidence